(-)-(S)-N-(6-Oxocyclohex-1-enyl)alanine ethyl ester | 182485-32-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (-)-(S)-N-(6-Oxocyclohex-1-enyl)alanine ethyl ester
• 英文别名: ethyl (2S)-2-[(6-oxocyclohexen-1-yl)amino]propanoate
• CAS: 182485-32-1
• 化学式: C₁₁H₁₇NO₃
• 分子量: 211.261
• InChiKey: MNJKZZUXHYPWKS-QMMMGPOBSA-N

物化性质

• 沸点：
  356.4±42.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-Nitropropen 、 (-)-(S)-N-(6-Oxocyclohex-1-enyl)alanine ethyl ester 反应 24.0h， 以30%的产率得到ethyl (2S)-2-(3-methyl-7-oxo-5,6-dihydro-4H-indol-1-yl)propanoate
  参考文献：
  名称：

  光学活性1,2,3-取代的-1,4,5,6-四氢-7 H-吲哚酮的合成†

  摘要：

  从共轭硝基烯烃和衍生自α-氨基酯和环己烷-1，2-二酮的α-酮烯胺通过一锅合成法获得三取代的1,4,5,6 ，-四氢-7 H-吲哚酮。在某些情况下，分离出双环[3.2.1] octan-8-one和1,2-恶嗪N-氧化物衍生物。

  DOI：

  10.1002/jhet.5570340106
• 作为产物：
  描述：

  (S,R,E)-N-(2-Oxocyclohexyl)alanine ethyl ester p-nitrophenylhydrazone 在 titanium(III) chloride 、 氧气 作用下， 以 氯仿 、 丙酮 为溶剂， 反应 2.0h， 生成 (-)-(S)-N-(6-Oxocyclohex-1-enyl)alanine ethyl ester
  参考文献：
  名称：

  Reactivity of conjugated azoalkenes towards α-amino acid ethyl esters

  摘要：

  The synthesis of Z- and E-arylhydrazones by 1,4-conjugate addition of glycine, L-alanine and L-tyrosine ethyl esters to phenylazostilbene 1, p-nitrophenylazostilbene 2 and p-nitrophenylazocyclohexene 3 is described. Optically active N-functionalized 2-aminocyclohexanones 22-26 are obtained by TiCl3-catalysed hydrolysis of the corresponding hydrazones. However, they have been shown to be unstable, as they undergo easy oxidation by air. X-Ray analysis of the phenylhydrazone 8a in the Z configuration is also reported.

  DOI：

  10.1039/p19960001961

文献信息

• Reactivity of conjugated azoalkenes towards α-amino acid ethyl esters
  作者：Silvano Bozzini、Fulvia Felluga、Giorgio Nardin、Alessandro Pizzioli、Giuliana Pitacco、Ennio Valentin

  DOI：10.1039/p19960001961

  日期：——

  The synthesis of Z- and E-arylhydrazones by 1,4-conjugate addition of glycine, L-alanine and L-tyrosine ethyl esters to phenylazostilbene 1, p-nitrophenylazostilbene 2 and p-nitrophenylazocyclohexene 3 is described. Optically active N-functionalized 2-aminocyclohexanones 22-26 are obtained by TiCl3-catalysed hydrolysis of the corresponding hydrazones. However, they have been shown to be unstable, as they undergo easy oxidation by air. X-Ray analysis of the phenylhydrazone 8a in the Z configuration is also reported.
• Synthesis of optically active 1,2,3-substituted-1,4,5,6-tetrahydro-7<i>H</i>-indolones
  作者：P. Nitti、G. Pitacco、A. Pizzioli、E. Valentin

  DOI：10.1002/jhet.5570340106

  日期：1997.1

  Trisubstituted 1,4,5,6,-tetrahydro-7H-indolones are obtained in a one-pot synthesis from conjugated nitroolefins and α-ketoenamines derived from α-amino esters and cyclohexane-1,2-dione. In some cases bicyclo[3.2.1]octan-8-one and 1,2-oxazine N-oxide derivatives are isolated.

  从共轭硝基烯烃和衍生自α-氨基酯和环己烷-1，2-二酮的α-酮烯胺通过一锅合成法获得三取代的1,4,5,6 ，-四氢-7 H-吲哚酮。在某些情况下，分离出双环[3.2.1] octan-8-one和1,2-恶嗪N-氧化物衍生物。